Book The Best Hotels in Far Southwest Side, IL for 2026 from CA $138 - Fully Refundable Options

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Our top choices for Far Southwest Side hotels

A modern hotel room with a large bed, a bedside table, a nightstand, and a wall-mounted light fixture.

A bathroom with a marble wall, a bathtub, a toilet, and a shower curtain.

A room with a window, a white shelf, a colorful striped rug, and a large number '6' on the wall.

1. Motel 6 - Chicago, IL

Washington Heights

Asia

CA $124

CA $146 total

includes taxes & fees

Sep 13 - Sep 14

A hotel room with a bed, a desk, a chair, a lamp, and a window with curtains.

A reception desk with various notices and a security camera.

A motel with a row of parking spaces and a building with a red roof and beige walls.

2. Saratoga Motel By Capital O Near Midway Airport Chicago IL

Ashburn

Roseanne

CA $119

CA $151 total

includes taxes & fees

Sep 14 - Sep 15

An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

A spacious outdoor dining area with large windows overlooking the sea, featuring multiple tables and stools.

A view from a room with a large window overlooking a cityscape at night, featuring a river and illuminated buildings.

A waterfront cityscape with modern buildings, a Ferris wheel, and several cruise ships docked.

3. Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Ashraf

CA $402

CA $526 total

includes taxes & fees

Sep 20 - Sep 21

A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

A spacious bar area with a central bar, multiple seating options including bar stools and tables, and a well-lit ceiling with recessed lighting.

Outdoor seating with yellow umbrellas labeled "Twisted Tea," wicker chairs, and tables.

A cityscape with various buildings, including a prominent skyscraper and a classical building with arched windows.

4. Congress Plaza Hotel

Downtown Chicago

Manuel

CA $227

CA $269 total

includes taxes & fees

Sep 27 - Sep 28

A large, historic building with a central courtyard surrounded by trees.

A restaurant interior with wooden tables and chairs, a carpeted floor, and framed pictures on the walls.

A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.

A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.

5. Hilton Chicago

Downtown Chicago

Lori

CA $313

CA $413 total

includes taxes & fees

Sep 25 - Sep 26

An outdoor seating area with wicker chairs, a glass-top table, and a sofa with cushions.

The exterior of the Hyatt Centric The Loop hotel with a prominent American flag, a classic facade, and a glass entrance.

A gym with multiple treadmills aligned in rows, a cityscape mural on the wall, and a view of the water outside.

A grilled pineapple on top of a stack of meat, served on a pan.

6. Hyatt Centric The Loop Chicago

Downtown Chicago

Tamika

CA $344

CA $443 total

includes taxes & fees

Sep 20 - Sep 21

A modern interior with a bar area, seating, and decorative wooden panels.

A reception area with a marble counter, decorative Buddha statues, and a wall with a quote.

A modern hotel with a prominent "Grant Park Hotel" sign and "Best Western" branding.

A hotel room with a flat-screen TV, a wooden cabinet, a round table, a blue sofa, a desk with a computer, and a large window with curtains.

7. Best Western Grant Park Hotel

Downtown Chicago

Diego

CA $247

CA $294 total

includes taxes & fees

Sep 29 - Sep 30

A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."

A bar area with a checkered floor, wooden chairs, a bar counter, and two televisions mounted on the wall.

A lobby with two green armchairs, a glass coffee table, a chandelier, and a fireplace.

A dimly lit restaurant with booths and tables, featuring a large clock and a television screen on the wall.

8. Carleton of Oak Park

Oak Park

Alan

CA $154

CA $171 total

includes taxes & fees

Oct 12 - Oct 13

A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.

A lobby with a checkered floor, an ATM, a potted plant, a reception desk, computers, and a staircase.

A restaurant with booths, tables, and a green wall in the background.

A hotel room with a bed, a desk with a chair, a sofa, and a view of a building through the window.

9. Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Matthew

CA $223

CA $265 total

includes taxes & fees

Sep 29 - Sep 30

A spacious lobby with a central coffee table, sofas, and a large mirror.

A spacious lounge area with leather sofas, round tables, and comfortable chairs, featuring a wooden ceiling and elegant decor.

A balcony with a table set for a meal, featuring a charcuterie board and two glasses of wine, overlooking a cityscape.

A spacious lobby with high ceilings, large arched windows, and a grand staircase.

10. The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Laura

CA $259

CA $308 total

includes taxes & fees

Sep 30 - Oct 1

A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.

A man in a suit sitting by a window with a vase of red flowers.

A hotel room with a grey sofa, a bed with a white mattress, a wooden dresser, and a large window with curtains.

A conference room with a long table, chairs, and a vase.

11. River Hotel

Downtown Chicago

steve

CA $206

CA $245 total

includes taxes & fees

Sep 27 - Sep 28

A modern hotel lobby with a reception desk, marble flooring, and elegant chandeliers.

A modern bar area with a bar counter, multiple stools, and a chandelier.

A modern living room with a dark sofa set, a glass coffee table, and a decorative chandelier.

A man and a woman walking down a marble staircase in a hotel lobby with a chandelier and a sign indicating an exit.

12. Silversmith Hotel Chicago Downtown

Downtown Chicago

Kun

CA $252

CA $342 total

includes taxes & fees

Sep 21 - Sep 22

An outdoor rooftop lounge with seating, a fire feature, and a view of the city skyline at night.

A rooftop venue with white chairs and a sofa, draped with white fabric and floral arrangements, overlooking a cityscape.

A modern lobby with a wooden ceiling, leather sofas, and a coffee bar.

A modern lounge area with leather sofas, wooden coffee tables, and ambient lighting.

13. The Chicago Hotel Collection - Magnificent Mile

Downtown Chicago

Patricia

CA $176

CA $210 total

includes taxes & fees

Sep 29 - Sep 30

An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

A modern hotel entrance with glass doors, a visible reception desk, and signage for Hilton Garden Inn and Homewood Suites.

A modern hotel lobby with a reception desk, seating area, and a large window providing a view of the outdoors.

A hot tub with a metal ladder, surrounded by white tiled walls and floor, with a large window providing a view of the cityscape.

14. Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Dhannetta

CA $315

CA $370 total

includes taxes & fees

Sep 21 - Sep 22

A cityscape at dusk with high-rise buildings, including a Hilton hotel.

A modern hotel lobby with a central seating area, a reception desk, and a cityscape mural on the wall.

A dining table set for a meal with a floral centerpiece, surrounded by chairs, in a room with a cityscape view.

A hotel room with a bed, a desk, a television, a sofa, and a large window with a city view.

15. Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Brian

CA $281

CA $334 total

includes taxes & fees

Oct 1 - Oct 2

A spacious bar area with high ceilings and large windows, offering views of a cityscape.

A bar with a circular liquor display, seating with stools, and a city view through large windows.

A multi-level hotel lobby with a glass elevator, a seating area, and a dining space.

A cityscape with modern high-rise buildings, a river, and a boat.

16. Hyatt Regency Chicago

Downtown Chicago

Steve

CA $407

CA $533 total

includes taxes & fees

Sep 26 - Sep 27

A modern lobby with a grey sofa, checkered ottomans, and a coffee table. There are black chairs, a blue sofa, and a TV on a stand.

A modern indoor swimming pool with blue seating and a view of the city through large windows.

A gym with treadmills, ellipticals, and weight machines.

A modern hotel room with a bed, a sofa, a coffee table with flowers, a TV, and a large window with a city view.

17. Aloft by Marriott Chicago Mag Mile

Downtown Chicago

Jerry

CA $248

CA $294 total

includes taxes & fees

Sep 20 - Sep 21

A historic building with a glass entrance, large columns, and decorative planters with flowers.

A spacious lobby with a checkered floor, colorful seating, and large windows.

A hotel lobby with a check-in counter, seating area, and a large potted plant.

A bar area with a variety of liquor bottles, a television screen, and colorful bar stools.

18. Warwick Allerton - Chicago

Downtown Chicago

Monique

CA $173

CA $247 total

includes taxes & fees

Oct 7 - Oct 8

A modern hotel room with two beds, a small table with glasses, a wall-mounted lamp, and a city view.

A modern living room with a grey sofa, a black armchair, a round coffee table with a book and a plant, and a large window with curtains.

A tall, multi-story building with a prominent vertical feature, likely a lobby or atrium, and a ground-level entrance with a green awning.

19. Hotel 55 Chicago Downtown

Downtown Chicago

Angel

CA $253

CA $342 total

includes taxes & fees

Sep 27 - Sep 28

A modern hotel lobby with grey upholstered chairs, a wooden coffee table, and a large window offering a view of the city and an American flag.

A tall, modern hotel with a brick facade and numerous windows.

20. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Downtown Chicago

Kelly

CA $250

CA $297 total

includes taxes & fees

Sep 27 - Sep 28

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Stay near popular Far Southwest Side attractions

Beverly Arts Center

Beverly Arts Center is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Make some time to visit the shops while you're in the area.

See properties

Highland Community Bank

Learn about the local history of Chicago when you take a trip to Highland Community Bank.

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Final Call Newspaper Headquarters

Find out about the history of Chicago with a stop at Final Call Newspaper Headquarters.

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Carter G. Woodson Library

You can enjoy some culture when you stop by Carter G. Woodson Library in Chicago. Make some time to visit the shops while you're in the area.

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Top Far Southwest Side Hotel Reviews

Hilton Chicago

10/10 Excellent

"My stay at the Chicago Hilton was truly exceptional. From the moment I arrived, I was impressed by the beautiful and elegant surroundings, outstanding amenities, and impeccable service. The staff were gracious, attentive, and professional, making the entire experience feel warm and welcoming. The hotel itself is absolutely gorgeous, with amenities that exceeded my expectations. I look forward to staying here again and would highly recommend the Chicago Hilton to anyone seeking a memorable and luxurious experience in Chicago."

Travelodge by Wyndham Downtown Chicago

10/10 Excellent

"TV didn't work"

Fairmont Chicago at Millennium Park

10/10 Excellent

"We had a wonderful two-night stay at Fairmont Chicago last weekend. We were so happy and pleasantly surprised when the hotel upgraded us to a beautiful suite. The suite was spacious, comfortable, and very nice, which made our stay even more special. We also really enjoyed the Gold Lounge. It was beautiful, comfortable, and offered a wonderful place to relax and enjoy food and drinks. The service was excellent, and everyone was friendly and welcoming. We truly enjoyed our stay and were very happy with our experience at Fairmont Chicago. We would definitely love to stay here again!"

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"Property was clean in perfect location. Close to restaurants, shopping, and the beach"

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"Room was comfortable & very clean. Staff was very accommodating."

Congress Plaza Hotel

8/10 Good

"My stay was great. But the hallway was off putting."

Warwick Allerton - Chicago

10/10 Excellent

"It was our first time in Chicago, and we would definitely stay here again. The hotel is clean, quiet, and so pretty. (with an art deco vibe) It’s also located in a great area, very easily walkable to most shops/attractions/etc that were already on our list. The staff was so friendly. I wish I got the name of the lovely lady who was so generous to my friends and I. Overall such a nice comfy place to stay at!"

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent

"I really liked the fact they had water stations with bottles you could fill up"

The Wade

8/10 Good

"Staff was friendly, bar was nice, but don’t go to Timmy’s for food or good drinks. And don’t drink the water in the room"

More cheap stays in Far Southwest Side

Quality Inn O'Hare Airport

3801 North Mannheim Road Schiller Park IL

CA $120

CA $138 total

Sep 27 - Sep 28

includes taxes & fees

7.6/10 Good! (2,340 reviews)

SureStay Plus Hotel by Best Western Chicago Lombard

222 E 22nd Street Lombard IL

CA $140

CA $155 total

Sep 28 - Sep 29

includes taxes & fees

Sleep Inn Midway Airport Bedford Park

6650 S Cicero Ave Chicago IL

CA $147

CA $172 total

Oct 5 - Oct 6

includes taxes & fees

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

CA $223

CA $265 total

Sep 29 - Sep 30

includes taxes & fees

7.6/10 Good! (2,828 reviews)

Holiday Inn Express Chicago - Magnificent Mile by IHG

640 N Wabash Ave Chicago IL

CA $275

CA $327 total

Sep 20 - Sep 21

includes taxes & fees

8.4/10 Very good! (1,329 reviews)

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

CA $281

CA $334 total

Sep 20 - Sep 21

includes taxes & fees

8/10 Very good! (1,596 reviews)

Hotels in Far Southwest Side with star rating

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Book Hotels in Far Southwest Side on Expedia.com

Find hotels in Far Southwest Side, IL from CA $138

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Far Southwest Side

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Far Southwest Side hotels

1. Motel 6 - Chicago, IL

2. Saratoga Motel By Capital O Near Midway Airport Chicago IL

3. Sable at Navy Pier Chicago, Curio Collection by Hilton

4. Congress Plaza Hotel

5. Hilton Chicago

6. Hyatt Centric The Loop Chicago

7. Best Western Grant Park Hotel

8. Carleton of Oak Park

9. Travelodge by Wyndham Downtown Chicago

10. The Chicago Hotel Collection Ambassador Gold Coast

11. River Hotel

12. Silversmith Hotel Chicago Downtown

13. The Chicago Hotel Collection - Magnificent Mile

14. Hilton Garden Inn Chicago Downtown South Loop

15. Hilton Chicago/Magnificent Mile Suites

16. Hyatt Regency Chicago

17. Aloft by Marriott Chicago Mag Mile

18. Warwick Allerton - Chicago

19. Hotel 55 Chicago Downtown

20. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Stay near popular Far Southwest Side attractions

Beverly Arts Center

Highland Community Bank

Final Call Newspaper Headquarters

Carter G. Woodson Library

Top Far Southwest Side Hotel Reviews

Hilton Chicago

Travelodge by Wyndham Downtown Chicago

Fairmont Chicago at Millennium Park

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection - Magnificent Mile

Congress Plaza Hotel

Warwick Allerton - Chicago

Club Quarters Hotel, Central Loop, Chicago

The Wade

More cheap stays in Far Southwest Side

Quality Inn O'Hare Airport

SureStay Plus Hotel by Best Western Chicago Lombard

Sleep Inn Midway Airport Bedford Park

Travelodge by Wyndham Downtown Chicago

Holiday Inn Express Chicago - Magnificent Mile by IHG

Hampton Inn Chicago Downtown/Magnificent Mile

Hotels in Far Southwest Side with star rating

Explore a world of travel with Expedia

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